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【结 构 式】 
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【分子编号】40581 【品名】 【CA登记号】 |
【 分 子 式 】C79H91Cl2N7O22Si 【 分 子 量 】1589.61642 【元素组成】C 59.69% H 5.77% Cl 4.46% N 6.17% O 22.14% Si 1.77% |
合成路线1
该中间体在本合成路线中的序号：(XXX)Selective debenzylation of (XXVI) with H2 over Pd/C with simultaneous reduction of its nitro group gives the primary alcohol (XXVII) with an amino group that is treated with t-Bu-ONO, Bu4NF and CuCl2 to obtain the corresponding chloro derivative (XXVIII). The oxidation of the primary alcohol of (XXVIII) with Dess Martin periodinane (DMP) and NaClO2 affords the expected carboxylic acid (XXIX), which is selectively deprotected at the Troc-NH group with Zn/Pb furnishing the free polycyclic polypeptide (XXX).
| 【1】 Boger, D.L.; et al.; First and second generation total synthesis of the teicoplanin aglycon. J Am Chem Soc 2001, 123, 9, 1862. |
| 【2】 Boger, D.L.; et al.; Total synthesis of the teicoplanin aglycon. J Am Chem Soc 2000, 122, 30, 7416. |
合成路线2
该中间体在本合成路线中的序号：(XXX)The cyclization of (XXX) by means of PyBop gives the complete teicoplanin ring assembly (XXXI), which is deprotected at the Mom-O-CH2 group with Br-catecholborane yielding the primary alcohol (XXXII), which is oxidized with Dess Martin periodinane (DMP) and NaClO2 to afford the corresponding carboxylic acid (XXXIII). Finally, (XXXIII) is fully deprotected with AlBr3/Et-S affording the target teicoplanin aglucon.
| 【1】 Boger, D.L.; et al.; First and second generation total synthesis of the teicoplanin aglycon. J Am Chem Soc 2001, 123, 9, 1862. |
| 【2】 Boger, D.L.; et al.; Total synthesis of the teicoplanin aglycon. J Am Chem Soc 2000, 122, 30, 7416. |